1-亚甲基-2-(2-甲基-1-丙烯基)环丙烷 | 103739-31-7

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 中文名称: 1-亚甲基-2-(2-甲基-1-丙烯基)环丙烷
• 英文名称: 1-methylene-2-(2-methyl-1-propenyl)cyclopropane
• 英文别名: 1-methylidene-2-(2-methylprop-1-enyl)cyclopropane
• CAS: 103739-31-7
• 化学式: C₈H₁₂
• 分子量: 108.183
• InChiKey: NQFLFJIOTPIYOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  8.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  (E)-2,5-dimethyl-1,3,5-hexatriene 生成 1-亚甲基-2-(2-甲基-1-丙烯基)环丙烷
  参考文献：
  名称：

  BROUWER, A. M.;JACOBS, H. J. C., TETRAHEDRON LETT., 1986, 27, N 12, 1395-1398

  摘要：

  DOI：

文献信息

• Spectroscopic characterization of 1-methylene-2-vinylcyclopropane and some of its derivatives
  作者：A. M. Brouwer、H. J. C. Jacobs

  DOI：10.1002/recl.19871060203

  日期：——

  show coupling patterns among the methylene and ring protons that are essentially independent of the substituents. The coupling constant between H-2 and the α-proton of the substituent depends on the conformation. 13C chemical shifts and coupling constants are readily interpreted using common substituent effect rules. MNDO calculations provide proton-proton distances and bond orders which are used to

  描述和讨论了1-亚甲基-2-乙烯基环丙烷1及其一些衍生物的特征NMR和振动光谱性质。持续地在1745cm -1处发现了外循环CC拉伸振动。的1 1 H NMR谱表明，基本上独立于所述取代基的亚甲基和环质子间偶合图案。H-2和取代基的α-质子之间的偶合常数取决于构象。使用常见的取代基效应规则可轻松解释13 C化学位移和偶联常数。MNDO计算提供了质子-质子距离和键序，用于解释质子弛豫率和质子-质子耦合常数。
• Wavelength effect on the photochemical reactions of (z)-2,5-dimethyl-1,3,5-hexatrene: selective excitation of rotamers
  作者：A.M. Brouwer、J. Cornelisse、H.J.C. Jacobs

  DOI：10.1016/s0040-4020(01)89975-0

  日期：1987.1

  5-hexatriene 1 is typical of a cZt triene, but the long wavelength tail Indicates the presence of the (minor) cZc rotamer. The sudden change In the photoreactivity of 1 around 290 nm is in agreement with selective excitation of these rotamers. No indication is obtained for an intrinsic excitation energy dependence of the photoreactivity of the Individual rotamers.

  Z-2,5-二甲基-1,3,5-己三烯1的UV吸收光谱是cZt三烯的典型特征，但长波长尾表明存在（次要）cZc旋转异构体。290 nm附近1的光反应性突然变化与这些旋转异构体的选择性激发相一致。没有获得关于单个旋转异构体的光反应性的内在激发能量依赖性的指示。
• Photochemistry of 2,5-dialkyl-1,3,5-hexatrienes. The influence of the ground-state conformation, controlled through steric substituent effects
  作者：A. M. Brouwer、L. Bezemer、J. Cornelisse、H. J. C. Jacobs

  DOI：10.1002/recl.19871061203

  日期：——

  The photochemical reactions of a number of 2,5-dialkyl-1,3,5-hexatrienes are described. Variations in the selectivity of the reactions are observed, which can be rationalized by considering differences in the composition of the equilibrium mixture of conformational isomers, brought about by steric substituent effects. This result is in agreement with the NEER principle. In addition, examples are given

  描述了许多2,5-二烷基-1,3,5-己三烯的光化学反应。观察到反应选择性的变化，这可以通过考虑由空间取代基效应引起的构象异构体的平衡混合物的组成差异来合理化。该结果与NEER原理一致。另外，给出了光诱导的异构化效率变化的实例，其不受NEER原理的限制。提出了一种涉及双自由基中间体的反应机理，该机理解释了所有包含三元环的反应产物的形成。MO相关图表明，作为主要步骤的三元环的形成必须以旋转方式发生。
• Photoreactions of (E)- and (Z)-2,5-dimethylhexatriene formation of a cyclopropene derivative: A novel reaction in triene photochemistry
  作者：A.M. Brouwer、H.J.C. Jacobs

  DOI：10.1016/s0040-4039(00)84268-9

  日期：1986.1

  reinvestigated. The previously observed short-wavelength irradiation product has been identified as 1-methyl-2-(2-methyl-2-propenyl)cyclopropene . The proposed intermediacy of a vinylcarbene in the formation of this novel type of product is supported by independent synthesis.

  Z，5-二甲基己三烯在254 nm处直接照射后获得的产物已被重新研究。先前观察到的短波长辐射产物已被鉴定为1-甲基-2-（2-甲基-2-丙烯基）环丙烯。独立合成支持了在该新型产物形成过程中拟议的乙烯基卡宾中间体。
• Conformational equilibrium and photochemistry of hexa-1,3,5-trienes
  作者：P.J. Vroegop、J. Lugtenburg、E. Havinga

  DOI：10.1016/s0040-4020(01)83160-4

  日期：1973.1